Charlie Clifford grew up a self-described "scrappy Jersey guy" in a town of 5,000 people, and won his first entrepreneurial prize in sixth grade: a watch, for out-hustling a classmate whose dad rigged the contest by buying magazine subscriptions wholesale for his medical office.

After business school at Indiana University, he joined one of the first Peace Corps pilot programs recruiting MBAs — sent to Peru to work with small businesses under a Stanford professor who'd later teach Nike's Phil Knight. He came home with $10,000, invested it in a scrappy import operation selling handcrafted South American leather goods, and in 1975 broke off to start his own company focused on travel bags. He named it TUMI, after a Peruvian ceremonial knife.

The brand's real breakthrough came when Clifford shifted from leather to black ballistic nylon — a fabric built for flak jackets — manufactured through a partnership with a small shop in Vidalia, Georgia. Bloomingdale's 59th Street flagship picking up the line put TUMI on the map. A conversation with a longtime retail partner, who told Clifford he had "so much product" he should just open his own stores, led to the "side-by-side" concept and eventually freestanding TUMI locations. By the 2000s, TUMI was the brand road warriors carried through airports worldwide, and it went public in 2012.

Clifford left the company in 2004, when the private equity partners who'd taken majority ownership after 9/11 decided to sell. He spent years distributing other people's luggage brands before realizing he wanted control over the product and the story again. In 2017, he and his former TUMI EVP Larry Lein founded ROAM — American-made, hand-assembled, and built around a philosophy that's the opposite of TUMI's black-on-black uniform: total color customization, so no two suitcases look the same.

Make sure to check out ROAM at: https://www.roamluggage.com/

And TUMI at: https://www.tumi.com/

Check out my new book on Amazon: https://amzn.to/4kRKGTX

Watch our mini-doc - Starting Small: The Raw Truth Behind Entrepreneurship and the American Dream: https://youtu.be/eHuq93wIxs0?si=eDB-ycngvWNapRLO

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This episode is brought to you by Panasonic. I just installed their WhisperGreen Select on a recent project, and I've gotta say — it's not what you picture when you think "bathroom fan." Panasonic's been in the ventilation game for decades, and this thing is proof. It's whisper quiet, ENERGY STAR certified, and you can customize it — airflow settings, LED lighting in five different color temperatures, even Wi-Fi and motion sensor add-ons if you want to get the best out of your new fan. It's a small detail in a home that makes a real difference. Make sure to check them out now at us.panasonic.com

Starting Small is powered by Riverside.fm, the AI-powered platform that lets you record, edit, repurpose,and distribute studio-quality content as easily as if you had a crew behind you. Check them out now at https://creators.riverside.com/CameronNagle

Adam Wexler played fantasy football since seventh grade — and turned that habit into a $4.15 billion exit. He built his first company out of a dorm room at the University of Georgia, launched a music discovery platform called Go Rankem in Athens, then pivoted into B2B SaaS with clients like Holiday Inn, IHG, Home Depot, UPS, and Coca-Cola before he ever touched sports.

In 2015, he incorporated Side Prize. When the fantasy sports market collapsed under regulatory pressure that same year, he rebuilt from a shoestring budget and relaunched in 2017 as PrizePicks — built on a "stupid simple" premise: get sports fans in and out of the app in under 60 seconds. He ran it as CEO for a decade, scaled it into the largest daily fantasy sports platform in North America, and in 2025 sold a majority stake to Allwyn International in a deal valued at up to $4.15 billion — without ever raising venture capital.

Rather than ride off into retirement, Wexler went back to where he started: music. He's now CEO of The Hidden Jams, a nonprofit platform funded by $5 million of his own money that crowdsources deep cuts and hidden gems from artist catalogs

Make sure to check out Prize Picks at: https://www.prizepicks.com/

And The Hidden Jams at: https://thehiddenjams.org/

Check out my new book on Amazon: https://amzn.to/4kRKGTX

Watch our mini-doc - Starting Small: The Raw Truth Behind Entrepreneurship and the American Dream: https://youtu.be/eHuq93wIxs0?si=eDB-ycngvWNapRLO

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Sound is one of those things that makes or breaks a hosting experience — and we finally got it right.

 We went with KICKER KB6 speakers mounted above the deck. Full-range, weather-resistant, built to throw sound across an open space without losing quality.

Kicker's been in the game since 1973 — car audio, marine, powersports — and they've expanded into Home & Personal audio, with headphones, earbuds and a complete line-up of outdoor audio speakers & subs. Engineered for performance, wherever you need sound.

If you're setting up an outdoor space for your home or business, and the audio isn't dialed in yet, start at Kicker.com.

Nick Stenson cut his first head of hair at 12 years old, in his mother's Chicago salon, with zero training and a customer's grandson in the chair. He was on track to become an orthopedic surgeon before realizing his mom was doing the same thing doctors do — changing how people carry themselves — one client at a time. He opened his first salon, Caviar Salons, in 2001, eventually running two locations and over 50 stylists. From there he became a creative director for L'Oréal and JCPenney Salons, styled Lady Gaga, Fergie, and Ashley Tisdale, and spent nine years at Ulta — starting with a team of seven and leaving as SVP of Services and Store Operations over a team of 400, after four promotions. In 2022 he launched Nick Stenson Beauty, a luxury haircare line built around aloe vera and creatine instead of ingredients nobody can pronounce. The brand is now sold at Ulta, Macy's, Nordstrom, and Amazon, with a professional distribution arm reaching salons nationwide. Twelve SKUs, all mix-and-matchable, no separate line for curly, straight, fine, or thick hair — just what your hair actually needs.

Make sure to check them out at: https://nickstensonbeauty.com

Check out my new book on Amazon: https://amzn.to/4kRKGTX

Watch our mini-doc - Starting Small: The Raw Truth Behind Entrepreneurship and the American Dream: https://youtu.be/eHuq93wIxs0?si=eDB-ycngvWNapRLO

Visit Starting Small Media: https://startingsmallmedia.org/

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Thank you to this episodes mid-break sponsor, Modern Shade.

They make hardtop gazebos, louvered pergolas, privacy screens, outdoor furniture — basically everything you need to take a backyard from functional to actually finished. Cedar wood, galvanized steel, aluminum — solid materials, well-designed structures across the board.

What we picked up are their Cedar Privacy Screens — great for adding side shade and privacy to a pergola or deck without blocking the whole view. Clean, natural look, does exactly what it should.

If your order's over $700, use code SS6 for 6% off. Check them out at ModernShade.org

One family recipe has grown into one of the fastest-rising brands in ready-to-drink cocktails. Inspired by her mother's gin, lemonade, and mint summer cooler, Meredith Mills-Merritt founded The Original Southside with a vision to bring premium ingredients, elevated branding, and transparency to a category that had long prioritized convenience over craftsmanship. Leveraging her background in prestige beauty, she obsessed over every detail—from developing a proprietary gin to creating a cocktail that's certified organic, vegan, gluten-free, and 10% ABV. That attention to detail has fueled remarkable growth.

Since launching in 2024, Southside has expanded into more than 20 markets, landed on shelves at Whole Foods and Total Wine, increased shipments by more than 370%, and continues its national expansion through Meijer, Rouses, and more than 90 additional Whole Foods locations. Beyond the product itself, Meredith is reshaping conversations around alcohol transparency as co-founder of the Clean Alcohol Collective, advocating for clearer ingredient standards across the industry.

Make sure to check them out at: https://www.drinksouthsides.com

Check out my new book on Amazon: https://amzn.to/4kRKGTX

Watch our mini-doc - Starting Small: The Raw Truth Behind Entrepreneurship and the American Dream: https://youtu.be/eHuq93wIxs0?si=eDB-ycngvWNapRLO

Visit Starting Small Media: https://startingsmallmedia.org/

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Thank you to this episodes mid-break sponsor, YETI. Summer is all about getting outside—whether that's hosting friends, firing up the grill, spending the day on the water, or packing up for a weekend away. That's why we've been using YETI. No matter where you're gathering, there's a YETI Hard Cooler built for the moment. We have the YETI Tundra 105, and it's been perfect for keeping food and drinks ice-cold through long days outside. Like every YETI Hard Cooler, it's built to handle just about anything, easy to haul wherever the crew is meeting, and designed with the legendary ice retention YETI is known for. If you're looking for a cooler that's built to last for years of adventures and backyard gatherings, check out the full YETI Hard Cooler collection at https://www.yeti.com/

Starting Small is powered by Riverside.fm, the AI-powered platform that lets you record, edit, repurpose,and distribute studio-quality content as easily as if you had a crew behind you. Check them out now at https://creators.riverside.com/CameronNagle

What started as two college friends chasing side hustles and building an Instagram account called @Sauce has grown into one of the most recognizable premium food brands in America. Today, TRUFF can be found in more than 17,000 retail locations nationwide, with an innovation pipeline stretching far beyond hot sauce.

Co-Founders Nick Guillen and Nick Ajluni join Starting Small to share how they set out to create the "Cîroc of hot sauce," spent nearly two years perfecting their original recipe, and turned a digitally native brand into a retail powerhouse. They unpack the early days of packing orders themselves, landing on Oprah's Favorite Things in year one, pioneering viral food content, and recently refreshing the brand with new packaging, Mild Sauce, and a line of Aioli & Dipping Sauces.

Make sure to check them out at: https://www.truff.com/

Check out my new book on Amazon: https://amzn.to/4kRKGTX

Watch our mini-doc - Starting Small: The Raw Truth Behind Entrepreneurship and the American Dream: https://youtu.be/eHuq93wIxs0?si=eDB-ycngvWNapRLO

Visit Starting Small Media: https://startingsmallmedia.org/

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Thank you to this episodes mid-break sponsor, Kichler Landscape.

For more than 85 years, Kichler has been designing lighting that doesn't just illuminate a space—it transforms it. And for over three decades, they've been pioneers in landscape lighting, creating some of the most comprehensive and innovative outdoor lighting solutions available today.

What I love about Kichler Landscape is that they think beyond simply putting lights in the ground. Their philosophy is all about intentional illumination—using layers of light to highlight architecture, showcase landscaping, create ambiance around gathering spaces, and make outdoor living feel just as inviting after sunset as it does during the day.

Visit Kichler.com and discover how thoughtfully designed lighting can completely transform the way you experience your home after dark.

Before Yes Way Rosé became one of the best-selling rosé brands in America, it started as an Instagram account.

Long before they sold a single bottle, Erica Small and Nikki Huganir were building a community around a simple idea: wine didn’t have to be intimidating. It could be fun, approachable, design-forward, and still be high quality.

That audience eventually became Yes Way Rosé.

Since launching the brand in 2018, the duo has sold more than 13 million bottles, grown into the fourth best-selling French rosé brand in the U.S., and expanded into sparkling, canned, and most recently, non-alcoholic rosé.

The newest launch was personal. After both becoming pregnant at the same time, Erica and Nikki searched for a non-alcoholic rosé that delivered the same experience as the French wines they loved. They couldn’t find one. So they spent nine months testing more than 50 formulations to create their own.

Make sure to check them out at: https://yeswayrose.com/

Check out my new book on Amazon: https://amzn.to/4kRKGTX

Watch our mini-doc - Starting Small: The Raw Truth Behind Entrepreneurship and the American Dream: https://youtu.be/eHuq93wIxs0?si=eDB-ycngvWNapRLO

Visit Starting Small Media: https://startingsmallmedia.org/

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Thank you to this episodes sponsors, Sylvox and The Best Adirondack Chair Company. You can find them below!

https://thebestadirondackchair.com/

https://sylvoxtv.com/

Angela Caglia spent decades behind the scenes as one of Hollywood’s most trusted estheticians before launching her own skincare brand. Her career started treating celebrity clients in Los Angeles, including Barbra Streisand, who once asked Angela what her dream was after a facial appointment at her home. Angela told her she wanted to create her own skincare line someday. Streisand’s response? “Why aren’t you doing it?” That moment stayed with her. After years building her reputation through hands-on treatments and opening her Bel Air spa, Angela launched Angela Caglia Skincare in 2016 — combining luxury spa treatments with regenerative skincare science. Most recently, the brand introduced its patent-pending Human-Derived Stem Cell Technology designed around exosomes, growth factors, and peptides aimed at supporting skin renewal at the cellular level. Her Cell Forté Serum quickly became the #1 selling serum in its category after launch, with unusually high subscription retention for a luxury skincare product. In this episode, Angela breaks down the evolution from celebrity esthetician to founder, how skincare has shifted from surface-level beauty to longevity and regeneration, and why trust matters more than trends in luxury wellness.

Make sure to check them out at: https://angelacaglia.com

Check out my new book on Amazon: https://amzn.to/4kRKGTX

Watch our mini-doc - Starting Small: The Raw Truth Behind Entrepreneurship and the American Dream: https://youtu.be/eHuq93wIxs0?si=eDB-ycngvWNapRLO

Visit Starting Small Media: https://startingsmallmedia.org/

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Thank you to this episodes sponsors, Backyard discovery,

Sylvox, and The Best Adirondack Chair Company. You can find them below!

https://thebestadirondackchair.com/

https://sylvoxtv.com/

https://www.backyarddiscovery.com/

Starting Small is powered by Riverside.fm, the AI-powered platform that lets you record, edit, repurpose,and distribute studio-quality content as easily as if you had a crew behind you. Check them out now at https://creators.riverside.com/CameronNagle

Long before SIMPLi hit shelves at Whole Foods, Sprouts, Erewhon, and Wegmans, Sarela and Matt were traveling globally working directly with farmers to source regenerative organic ingredients and rebuild transparency at the root level of food production. What started as a sourcing mission eventually became SIMPLi — a pantry brand focused on traceability, regenerative agriculture, and proving that better food systems can scale without cutting corners. In this episode, Sarela and Matt break down how they built relationships with farming communities around the world, why most consumers have no idea where their pantry staples actually come from, and what it takes to create a mission-driven food brand in a category dominated by massive incumbents.

Make sure to check them out at: https://eatsimpli.com

Check out my new book on Amazon: https://amzn.to/4kRKGTX

Watch our mini-doc - Starting Small: The Raw Truth Behind Entrepreneurship and the American Dream: https://youtu.be/eHuq93wIxs0?si=eDB-ycngvWNapRLO

Visit Starting Small Media: https://startingsmallmedia.org/

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LinkedIn: http://linkedin.com/in/cameronnagle

Terramor is a luxury glamping resort with 64 upscale tent accommodations tucked into the woods near Acadia National Park. The food was incredible, the amenities were dialed in, and their guy, Omar,  took us through this private saltwater immersion experience in nature that I did not see coming — cold, but completely shifted my body and mind - followed by a robe and hot tea right on the ocean.

It's one of those places where you're fully immersed in nature, but you're not sacrificing comfort. You just... decompress.

If that sounds like something you need right now, go check them out, they’re open May-October and whether with the family, special event,couples retreat… you have to take my word on this experience— TerramorOutdoorResort.com.

Lauren Corugedo grew up watching Chef Merito operate like a hidden gem in Los Angeles kitchens long before the rest of the country caught on. Founded in 1985 by her Cuban immigrant grandfather, Chef Merito started with a single carne asada seasoning and built a loyal following through word of mouth, neighborhood markets, and authentic flavor that didn’t compromise to fit trends. Now, nearly 40 years later, the brand has expanded far beyond Southern California — landing in Costco, Amazon, major retailers, and even Dodger Stadium — while still staying rooted in the same recipes and cultural identity that built it in the first place. In this episode, Lauren shares what it’s like stepping into a second-generation family business, modernizing a legacy brand for a new generation of consumers, and balancing growth without losing authenticity.

Make sure to check them out at: https://chefmerito.com

Check out my new book on Amazon: https://amzn.to/4kRKGTX

Watch our mini-doc - Starting Small: The Raw Truth Behind Entrepreneurship and the American Dream: https://youtu.be/eHuq93wIxs0?si=eDB-ycngvWNapRLO

Visit Starting Small Media: https://startingsmallmedia.org/

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Dr. Kyle Landry wasn’t trying to build another skincare brand. Before Delavie Sciences, he was doing postdoctoral research at Harvard studying extremophiles — organisms capable of surviving radiation, extreme heat, and even the vacuum of space. That research eventually led him to a microorganism connected to NASA and the International Space Station that could withstand conditions most life forms couldn’t.' What started as a government and biosecurity research project turned into something completely different: a patented skincare ingredient called Bacillus Lysate. Today, that ingredient sits at the center of Delavie Sciences — a company bringing space-tested biotechnology into consumer skincare. Their Aeonia serum became the first biological cosmetic recognized as Certified Space Technology™, with studies showing major increases in hyaluronic acid production, hydration, and skin elasticity.

Make sure to check them out at: https://www.delaviesciences.com

Check out my new book on Amazon: https://amzn.to/4kRKGTX

Watch our mini-doc - Starting Small: The Raw Truth Behind Entrepreneurship and the American Dream: https://youtu.be/eHuq93wIxs0?si=eDB-ycngvWNapRLO

Visit Starting Small Media: https://startingsmallmedia.org/

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